title: Metabolites from the endophytic [corrected] fungus Sporormiella minimoides isolated from Hintonia latiflora.
abstract: An extract of the solid cultures of Sporormiella minimoides (Sporormiaceae) isolated as an endophytic fungus from Hintonia latiflora (Rubiaceae), yielded three polyketides, 3,6-dimethoxy-8-methyl-1H,6H-benzo[de]isochromene-1,9-dione, 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3H-benzo[de]isochromen-9-one, and 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone, along with three known compounds, corymbiferone, ziganein, and brocaenol B. Their structures were characterized by spectrometric and spectroscopic methods. So as to be consistent the literature reports, 3,6-dimethoxy-8-methyl-1H,6H-benzo[de]isochromene-1,9-dione and 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3H-benzo[de]isochromen-9-one were given the trivial names of corymbiferone C and corymbiferan lactone E, respectively. All isolates were tested as potential human calmodulin (hCaM) inhibitors using the fluorescent biosensor hCaM V91C-mBBr, but only 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone quenched significantly the extrinsic fluorescence of this biosensor, with a dissociation constant (Kd) value of 1.55 μM. Refined docking analysis predicted that 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone could also be bound to hCaM at site I displaying hydrophobic interactions with Phe19 and 68, Met51, 71, and 72, and Ile52 and 63 residues.
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, México DF 04510, Mexico.
authors.forename: Martha
authors.initials: M
authors.lastname: Leyte-Lugo
authors.forename: Mario
authors.initials: M
authors.lastname: Figueroa
authors.forename: María del Carmen
authors.initials: Mdel C
authors.lastname: González
authors.forename: Anthony E
authors.initials: AE
authors.lastname: Glenn
authors.forename: Martín
authors.initials: M
authors.lastname: González-Andrade
authors.forename: Rachel
authors.initials: R
authors.lastname: Mata
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds; D002147:Calmodulin / Q000037:antagonists & inhibitors*; D006801:Humans; D008956:Models, Chemical; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019666:Rubiaceae / Q000737:chemistry / Q000382:microbiology*
chemical_list: C000589058:3,6-dimethoxy-8-methyl-1H,6H-benzo(de)isochromene-1,9-dione; C000589059:3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3H-benzo(de)isochromen-9-one; C000589060:5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone; D001643:Bridged Bicyclo Compounds; D002147:Calmodulin; D009285:Naphthoquinones; D061065:Polyketides; C028381:monobromobimane
keywords: Calmodulin inhibitors; Endophytic fungus; Hintonia latiflora; Polyketides; Sporormiella minimoides